Rockport, Massachusetts: Great Day Trip from Boston

Massachusetts is undeniably beautiful in summer. Areas like Cape Cod and Martha’s Vineyard are particularly famous because that’s where many of the wealthy and powerful vacation. But summer traffic and accommodation prices in those areas can be heavy and steep respectively. If you want to get better bang for your buck and time, consider driving north of Boston, to beautiful Rockport, Massachusetts on Cape Ann.

On the way to Rockport, there’s several other noteworthy towns. The most famous is Salem, famous for the witchcraft trials in 1692. Salem is just 22 miles north of Boston and offers interesting tours, shopping, good eateries and historical significance. And these days, nobody will torture you for being a “witch!”

From Salem you can take a lovely coastal drive along Cape Ann on Highway 127. But if you have limited time or want to eventually continue north along the scenic New Hampshire and Maine coast, jump on the Yankee Division Highway to arrive in Rockport quicker. Just a few miles from Rockport, Gloucester is another town of historical significance. Gloucester was America’s original seaport and home to the nation’s oldest working art colony. You can even see lighthouses dating back to the 1780’s.

Rockport itself is a gem, just 39 miles north of Boston, Bostonians in the know love this town. We enjoyed watching a gorgeous sunset from the beach, looking across a quintessentially rocky New England coast. Rockport is loaded with an abundance of cute and historic buildings housing shops, restaurants and ice cream shops.

New England takes ice cream seriously, and Rockport’s adorable Ice Cream Store is no exception. There were a lot of interesting and high quality flavors to choose from. Maple walnut is usually an excellent choice because, in New England, almost anything with maple syrup is great!

Delicious Seafood in Rockport Massachusetts

We enjoyed a fantastic dinner at Roy Moore’s Fish Shack, with a wonderful view of the sunset over Rockport. Their crab cakes were as good as any we’ve ever eaten. You’ll be hard pressed to top a delicious $10 crab cake main with two sides anywhere. Their fish tacos were also tasty, but the crab cakes were the highlight. Like any good seafood restaurant in the northeast, whole lobsters, as well as lobster rolls are popular items on the menu.

There’s a lot to love about Rockport Massachusetts and Cape Ann. And if you’ve never seen the autumn foliage in New England it’s something you should add to your bucket list. There’s so many great spots in New England to enjoy that, including the rolling hills of western Massachusetts.

If you’re looking to plan a trip to Boston and travel around New England, contact alex@wanderlustmarriage.com. Inquire about great prices for customized itineraries that will save you money on plane tickets and accommodation!

Living in Boston, we’ve been to both Gloucester and Rockport and thoroughly loved both these towns 🙂 There’s a bakery called Helmut’s Strudel shop that serves the most delicious apple strudels – we particularly remember this place! Thanks for the tip about getting to Rockport quicker – will surely keep that in mind!

Your photos are beautiful! The sky, the shore, all of it just comes together, and Rockport certainly lives up to its name! The crab cakes sound so good, and this just seems like an all-around awesome day trip.

Thank you for the compliment on our photos! It was lovely to be in Rockport for sunset. The long days in summer make it possible to get there in the evening after a work day during the week, like this visit for crab cakes!

I never made it to Rockport over the years I visited Boston. Gloucester was a favorite spot though and I had relatives living in that art colony at the time. It was fun to hang out there winter or summer.

My husband and I are flying in to Boston this September, spending a couple days there, then driving down the coast (with many stops along the way), ending at the Chesapeake Bay. When I was researching charming coastal towns, Rockport came up, but I initially deleted it from our itinerary since it’s north of Boston and we’re traveling south. Then I saw a suggestion of doing a day trip to Rockport from Boston, which would mean we’d stay overnight in Boston an additional night. In your opinion, if we’re visiting the Cape, Nantucket, Newport, Cape May, and more, is Rockport worth an extra day trip in the opposite direction when our time is limited? Or should we skip on this trip?

Hi Hollie, good question. Rockport’s a lovely town, but as you will be visiting so much of the Cape and beyond, with limited time, perhaps there’s no need to backtrack. If you’re going to be taking smaller roads along your journey down to Chesapeake Bay, the driving might take longer than you anticipate, especially with traffic. Sometimes less is more and that will allow you two to get to know all the beautiful destinations you visit a little better. Let us know if you have additional questions. Happy planning and we wish you a wonderful trip!